Heatherkellyproperties.com Search Results

$5,225,000

Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor shower, parking, and mini-split climate control; its upstairs bedroom enjoys views from Farm Pond to Nantucket Sound. Completing the property is the charming Lilac House, a fun open-concept bunk house with a full bath, water-view deck, and private outdoor shower. A wraparound porch captures sweeping ocean views, while beaches, shops, restaurants, Circuit Avenue, and the Harbor are moments away. An established rental history further enhances this rare opportunity in one of Oak Bluffs’ most iconic locations.

6 Beds ⋅ 4 Baths

Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor shower, parking, and mini-split climate control; its upstairs bedroom enjoys views from Farm Pond to Nantucket Sound. Completing the property is the charming Lilac House, a fun open-concept bunk house with a full bath, water-view deck, and private outdoor shower. A wraparound porch captures sweeping ocean views, while beaches, shops, restaurants, Circuit Avenue, and the Harbor are moments away. An established rental history further enhances this rare opportunity in one of Oak Bluffs’ most iconic locations.

4 Canonicus Ave, Oak Bluffs

Listing Courtesy of : Katie Donahue & Rachel Serwa Group ---- Sandpiper Realty, Inc.

$5,200,000

Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.

5 Beds ⋅ 4 Baths

Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.

49 Gosnolds Way, Chilmark

Listing Courtesy of : Bonnie Pierce ---- Wallace & Co. Sotheby's International Realty

$5,200,000

A rare Lake Winnipesaukee offering, this legacy property features 300 feet of pristine waterfront and over 2.7 private acres and spectacular views, ideally situated between Meredith and Center Harbor, providing convenient access to shopping, dining, marinas, and all the attractions of the Lakes Region. Turn into the beautiful winding driveway and shortly you will be at home. Blending classic lakehouse charm with modern amenities, this inviting waterfront retreat is designed for gathering and making memories. The spacious kitchen is a chef's dream, featuring an 8-burner Viking range, walk-in pantry, wet bar, and ample space for entertaining. Multiple living areas, highlighted by two fireplaces, offer comfortable places to relax in every season, while the screened porch provides the perfect setting for morning coffee or evening dinners overlooking the lake. The main level includes a bedroom and ¾ bath, offering flexibility for guests and convenient first-floor living. Upstairs, the primary suite enjoys its own large private deck with sweeping water views, accompanied by two additional bedrooms and a full bath. Beautifully landscaped grounds lead to the waterfront, where two private docks, walk-in lake access, with sandy bottom and 300 feet of shoreline create an exceptional setting for boating, swimming, and enjoying life on the lake. An adorable bunkhouse with its own screened porch and ¾ bath provides a charming guest retreat just steps from the water. Additional features include a detached two-car garage with a screened porch and finished space above, as well as a detached barn offering abundant storage for boats, water toys, and recreational equipment. Combining exceptional privacy, extensive waterfrontage, and close proximity to everything by car or by boat, this is a unique opportunity to own a classic Lake Winnipesaukee property ready to be enjoyed for generations to come. 6 BR State approved septic.

5 Beds ⋅ 4 Baths

A rare Lake Winnipesaukee offering, this legacy property features 300 feet of pristine waterfront and over 2.7 private acres and spectacular views, ideally situated between Meredith and Center Harbor, providing convenient access to shopping, dining, marinas, and all the attractions of the Lakes Region. Turn into the beautiful winding driveway and shortly you will be at home. Blending classic lakehouse charm with modern amenities, this inviting waterfront retreat is designed for gathering and making memories. The spacious kitchen is a chef's dream, featuring an 8-burner Viking range, walk-in pantry, wet bar, and ample space for entertaining. Multiple living areas, highlighted by two fireplaces, offer comfortable places to relax in every season, while the screened porch provides the perfect setting for morning coffee or evening dinners overlooking the lake. The main level includes a bedroom and ¾ bath, offering flexibility for guests and convenient first-floor living. Upstairs, the primary suite enjoys its own large private deck with sweeping water views, accompanied by two additional bedrooms and a full bath. Beautifully landscaped grounds lead to the waterfront, where two private docks, walk-in lake access, with sandy bottom and 300 feet of shoreline create an exceptional setting for boating, swimming, and enjoying life on the lake. An adorable bunkhouse with its own screened porch and ¾ bath provides a charming guest retreat just steps from the water. Additional features include a detached two-car garage with a screened porch and finished space above, as well as a detached barn offering abundant storage for boats, water toys, and recreational equipment. Combining exceptional privacy, extensive waterfrontage, and close proximity to everything by car or by boat, this is a unique opportunity to own a classic Lake Winnipesaukee property ready to be enjoyed for generations to come. 6 BR State approved septic.

28 Veasey Shore Rd, Meredith

Listing Courtesy of : Ellen Mulligan ---- Coldwell Banker Realty Center Harbor NH Off: 603-253-4345

$5,195,000

Offering an elegant lifestyle without compromise, this property spans 1.24 acres and boasts stunning ocean views, perfect for both grand celebrations and serene retreats. An array of five-star amenities enhances the private compound: an outdoor heated pool, a cabana bar with a television and grill, a putting green, an elevator, and an ocean-viewing platform with a private staircase to rugged Pint Cove. The first floor boasts open living areas that offer breathtaking views framed by expansive walls of windows. French doors lead to the covered seating and to the open sun deck, perfect for alfresco dining. The coastal ambiance is highlighted throughout the living area, with maple flooring, elegant, coffered ceilings, and a gas fireplace surrounded by handsome built-ins, raised paneling, and polished stone slabs. Ideal for gourmet cooking, the kitchen showcases an island with bar seating, a brushed stainless-steel refrigerator, an oversized gas range with double ovens, and custom cabinetry. Additional features on the first floor include a billiard room with bar, a screened-in seaside porch, a private entry guest suite, and an office with a nearby bathroom. The grand turret staircase, featuring elegant, twisted balustrades and a custom wood tray ceiling, leads to the generous primary suite. It includes a spacious living area with a wet bar and beverage refrigerator, a gas fireplace, and a door leading to a romantic balcony overlooking the sea. Double vanities, a large, jetted tub, and a separate custom-tiled shower define the primary bath. This level offers two additional guest suites and a gym nook. Downstairs, the media room features tiered theater seating, a wet bar with two beverage refrigerators, and a bar island. The temperature-controlled wine cellar features backlit wine storage and a tasting table, as well as a bathroom and ample storage. The garage offers custom closets for additional organization. Sandy Cape Neddick beach is a stroll away.

4 Beds ⋅ 6 Baths

Offering an elegant lifestyle without compromise, this property spans 1.24 acres and boasts stunning ocean views, perfect for both grand celebrations and serene retreats. An array of five-star amenities enhances the private compound: an outdoor heated pool, a cabana bar with a television and grill, a putting green, an elevator, and an ocean-viewing platform with a private staircase to rugged Pint Cove. The first floor boasts open living areas that offer breathtaking views framed by expansive walls of windows. French doors lead to the covered seating and to the open sun deck, perfect for alfresco dining. The coastal ambiance is highlighted throughout the living area, with maple flooring, elegant, coffered ceilings, and a gas fireplace surrounded by handsome built-ins, raised paneling, and polished stone slabs. Ideal for gourmet cooking, the kitchen showcases an island with bar seating, a brushed stainless-steel refrigerator, an oversized gas range with double ovens, and custom cabinetry. Additional features on the first floor include a billiard room with bar, a screened-in seaside porch, a private entry guest suite, and an office with a nearby bathroom. The grand turret staircase, featuring elegant, twisted balustrades and a custom wood tray ceiling, leads to the generous primary suite. It includes a spacious living area with a wet bar and beverage refrigerator, a gas fireplace, and a door leading to a romantic balcony overlooking the sea. Double vanities, a large, jetted tub, and a separate custom-tiled shower define the primary bath. This level offers two additional guest suites and a gym nook. Downstairs, the media room features tiered theater seating, a wet bar with two beverage refrigerators, and a bar island. The temperature-controlled wine cellar features backlit wine storage and a tasting table, as well as a bathroom and ample storage. The garage offers custom closets for additional organization. Sandy Cape Neddick beach is a stroll away.

1 Cove Rd, York

Listing courtesy of Anne Erwin Sotheby's International Realty. 207-363-6640

$5,195,000

Experience the pinnacle of luxury living with this breathtaking waterfront estate on Long Lake. Nestled on an expansive private lot with 800 feet of pristine shoreline, this extraordinary property offers a sandy beach, private dock, and a stunning boardwalk, creating the ultimate lakeside retreat. The 5,122 sq. ft. custom-designed main home features 4 bedrooms and 4.5 bathrooms, showcasing impeccable craftsmanship and high-end finishes throughout. Step into the grand living room, where cathedral ceilings and a dramatic floor-to-ceiling stone fireplace set the tone for elegant relaxation. Walls of floor-to-ceiling windows frame breathtaking panoramic lake views, bathing the home in natural light. A gourmet chef's kitchen, adorned with rich stonework and premium appliances, makes entertaining effortless. The luxurious primary en-suite offers a serene escape with a double-sided fireplace, spa-inspired bath, and a private balcony overlooking the water. Beautiful multi-functional den/office/bedroom with full bath, floor to ceiling windows and built-ins. This property includes an attached 3-car garage and a detached 3-car carriage house topped with a 1,384 sqft, 2 bedroom open concept in-law suite with a beautiful full kitchen and center island, perfect for guests or multi-generational living. Blending timeless elegance with modern luxury, this Long Lake masterpiece offers an unparalleled waterfront lifestyle. Ideal for both private enjoyment and lavish entertaining.

6 Beds ⋅ 6 Baths

Experience the pinnacle of luxury living with this breathtaking waterfront estate on Long Lake. Nestled on an expansive private lot with 800 feet of pristine shoreline, this extraordinary property offers a sandy beach, private dock, and a stunning boardwalk, creating the ultimate lakeside retreat. The 5,122 sq. ft. custom-designed main home features 4 bedrooms and 4.5 bathrooms, showcasing impeccable craftsmanship and high-end finishes throughout. Step into the grand living room, where cathedral ceilings and a dramatic floor-to-ceiling stone fireplace set the tone for elegant relaxation. Walls of floor-to-ceiling windows frame breathtaking panoramic lake views, bathing the home in natural light. A gourmet chef's kitchen, adorned with rich stonework and premium appliances, makes entertaining effortless. The luxurious primary en-suite offers a serene escape with a double-sided fireplace, spa-inspired bath, and a private balcony overlooking the water. Beautiful multi-functional den/office/bedroom with full bath, floor to ceiling windows and built-ins. This property includes an attached 3-car garage and a detached 3-car carriage house topped with a 1,384 sqft, 2 bedroom open concept in-law suite with a beautiful full kitchen and center island, perfect for guests or multi-generational living. Blending timeless elegance with modern luxury, this Long Lake masterpiece offers an unparalleled waterfront lifestyle. Ideal for both private enjoyment and lavish entertaining.

3 & 4 Trestle Ln, Harrison

Listing courtesy of Landing Real Estate.

$5,195,000

Offering an elegant lifestyle without compromise, this property spans 1.24 acres and boasts stunning ocean views, perfect for both grand celebrations and serene retreats. An array of five-star amenities enhances the private compound: an outdoor heated pool, a cabana bar with a television and grill, a putting green, an elevator, and an ocean-viewing platform with a private staircase to rugged Pint Cove. The first floor boasts open living areas that offer breathtaking views framed by expansive walls of windows. French doors lead to the covered seating and to the open sun deck, perfect for alfresco dining. The coastal ambiance is highlighted throughout the living area, with maple flooring, elegant, coffered ceilings, and a gas fireplace surrounded by handsome built-ins, raised paneling, and polished stone slabs. Ideal for gourmet cooking, the kitchen showcases an island with bar seating, a brushed stainless-steel refrigerator, an oversized gas range with double ovens, and custom cabinetry. Additional features on the first floor include a billiard room with a six-stool bar, an adjacent screened-in seaside porch, a guest suite with private deck access, and an overflow guest room with a nearby bathroom. The grand turret staircase, featuring elegant, twisted balustrades and a custom wood tray ceiling, leads to the generous primary suite. It includes a spacious living area with a wet bar and beverage refrigerator, a gas fireplace, and a door leading to a romantic balcony overlooking the sea. Double vanities, a large, jetted tub, and a separate custom-tiled shower define the primary bath. This level offers two additional guest suites and a workout nook. Downstairs, the media room features tiered theater seating, a wet bar with two beverage refrigerators, and a bar island. The temperature-controlled wine cellar features backlit wine storage and a tasting table, as well as a bathroom and ample storage. The garage comes with custom closets for additional organization.

4 Beds ⋅ 6 Baths

Offering an elegant lifestyle without compromise, this property spans 1.24 acres and boasts stunning ocean views, perfect for both grand celebrations and serene retreats. An array of five-star amenities enhances the private compound: an outdoor heated pool, a cabana bar with a television and grill, a putting green, an elevator, and an ocean-viewing platform with a private staircase to rugged Pint Cove. The first floor boasts open living areas that offer breathtaking views framed by expansive walls of windows. French doors lead to the covered seating and to the open sun deck, perfect for alfresco dining. The coastal ambiance is highlighted throughout the living area, with maple flooring, elegant, coffered ceilings, and a gas fireplace surrounded by handsome built-ins, raised paneling, and polished stone slabs. Ideal for gourmet cooking, the kitchen showcases an island with bar seating, a brushed stainless-steel refrigerator, an oversized gas range with double ovens, and custom cabinetry. Additional features on the first floor include a billiard room with a six-stool bar, an adjacent screened-in seaside porch, a guest suite with private deck access, and an overflow guest room with a nearby bathroom. The grand turret staircase, featuring elegant, twisted balustrades and a custom wood tray ceiling, leads to the generous primary suite. It includes a spacious living area with a wet bar and beverage refrigerator, a gas fireplace, and a door leading to a romantic balcony overlooking the sea. Double vanities, a large, jetted tub, and a separate custom-tiled shower define the primary bath. This level offers two additional guest suites and a workout nook. Downstairs, the media room features tiered theater seating, a wet bar with two beverage refrigerators, and a bar island. The temperature-controlled wine cellar features backlit wine storage and a tasting table, as well as a bathroom and ample storage. The garage comes with custom closets for additional organization.

1 Cove Rd, York

Listing Courtesy of : Anne Erwin Real Estate ---- Anne Erwin Sothebys International Rlty Call/text 207-370-5406? for info

$5,150,000

Thirteen Foreside Road is a classic Falmouth Foreside estate designed by revered Maine architect John Calvin Stevens. Built in 1925 as a summer residence and historically known as ''Fairways,'' the home is set on over 4 acres beside the Portland Country Club, with views across the Donald Ross-designed golf course toward Casco Bay. A long, winding, tree-lined gravel road creates a memorable sense of arrival, setting the tone for the property's old-world charm and quiet sense of seclusion. Thoughtfully updated by Palm Beach-based Stephanie Rae Interiors and Bloom Construction, the residence blends historic architectural character with a refined, modern sensibility. The home offers 5 bedrooms, 5 full bathrooms, and 1 half bathroom, including a first-floor bedroom suite and four additional bedrooms on the second level. Generous room proportions, wood floors, natural light, and a comfortable flow create a sense of ease throughout. The first floor includes a gracious living room with a wood-burning fireplace, a formal dining room with French doors, and a beautifully appointed kitchen centered around a marble island with a handmade butcher block. A butler's pantry adds function and style, while the four-season sunroom offers southern exposure and views across the fairways toward Casco Bay. Upstairs, the primary suite includes a soaking tub and walk-in closet, with additional bedrooms, baths, office space, and flexible bonus areas for guests, work, and everyday living. The former three-car garage has since been rebuilt into a finished office space and home gym. Outside, mature landscaping, wooded surroundings, and established grounds create a timeless setting in the heart of Falmouth Foreside. Just moments from Portland Country Club, Falmouth amenities, Route 1, and downtown Portland, Thirteen Foreside Road offers a rare combination of architectural pedigree, acreage, privacy, and convenience.

5 Beds ⋅ 6 Baths

Thirteen Foreside Road is a classic Falmouth Foreside estate designed by revered Maine architect John Calvin Stevens. Built in 1925 as a summer residence and historically known as ''Fairways,'' the home is set on over 4 acres beside the Portland Country Club, with views across the Donald Ross-designed golf course toward Casco Bay. A long, winding, tree-lined gravel road creates a memorable sense of arrival, setting the tone for the property's old-world charm and quiet sense of seclusion. Thoughtfully updated by Palm Beach-based Stephanie Rae Interiors and Bloom Construction, the residence blends historic architectural character with a refined, modern sensibility. The home offers 5 bedrooms, 5 full bathrooms, and 1 half bathroom, including a first-floor bedroom suite and four additional bedrooms on the second level. Generous room proportions, wood floors, natural light, and a comfortable flow create a sense of ease throughout. The first floor includes a gracious living room with a wood-burning fireplace, a formal dining room with French doors, and a beautifully appointed kitchen centered around a marble island with a handmade butcher block. A butler's pantry adds function and style, while the four-season sunroom offers southern exposure and views across the fairways toward Casco Bay. Upstairs, the primary suite includes a soaking tub and walk-in closet, with additional bedrooms, baths, office space, and flexible bonus areas for guests, work, and everyday living. The former three-car garage has since been rebuilt into a finished office space and home gym. Outside, mature landscaping, wooded surroundings, and established grounds create a timeless setting in the heart of Falmouth Foreside. Just moments from Portland Country Club, Falmouth amenities, Route 1, and downtown Portland, Thirteen Foreside Road offers a rare combination of architectural pedigree, acreage, privacy, and convenience.

13 Foreside Rd, Falmouth

Listing courtesy of Legacy Properties Sotheby's International Realty.

$5,100,000

Two hundred and twenty-three feet on Casco Bay, a deep-water dock, and views that reach Eagle Island, Egg Rock Lighthouse, Bustins Island, and Harpswell Point. An osprey pair nests on the property each year. On Wednesday evenings in the spring and summer, there are sailboat races you can view from the deck or the dock. Built in 2012, this 5-bedroom, 6-bath shingle-style Colonial sits on 2.51 acres. The main living level is anchored by a stone fireplace and hardwood floors, with windows positioned to hold the view from nearly every room. The kitchen connects openly to the living space and functions as the center of the home. Five bedrooms, including a main-floor primary suite with direct bay views. Finished lower-level adds an exercise room and flex space. Zoning allows for additional structures on the acreage. Wolfe's Neck Woods State Park is one mile away. Wolfe's Neck Farm, trails, and learning center is two miles.

5 Beds ⋅ 8 Baths

Two hundred and twenty-three feet on Casco Bay, a deep-water dock, and views that reach Eagle Island, Egg Rock Lighthouse, Bustins Island, and Harpswell Point. An osprey pair nests on the property each year. On Wednesday evenings in the spring and summer, there are sailboat races you can view from the deck or the dock. Built in 2012, this 5-bedroom, 6-bath shingle-style Colonial sits on 2.51 acres. The main living level is anchored by a stone fireplace and hardwood floors, with windows positioned to hold the view from nearly every room. The kitchen connects openly to the living space and functions as the center of the home. Five bedrooms, including a main-floor primary suite with direct bay views. Finished lower-level adds an exercise room and flex space. Zoning allows for additional structures on the acreage. Wolfe's Neck Woods State Park is one mile away. Wolfe's Neck Farm, trails, and learning center is two miles.

675 Wolfes Neck Rd, Freeport

Listing courtesy of Legacy Properties Sotheby's International Realty.

$5,100,000

Situated on a lovely street, this very special five story townhome has it all. There are three plus bedrooms with potential for more as the top floor with an open floor plan and sunny balcony offers great flexibility. Wonderful entertaining space and formal rooms with beautiful proportions and architectural details add to the charm. A door from the living room opens out to an extraordinary deck with a balustrade. The bright, eat-in kitchen with large windows looks out on the inviting garden. Amenities include a finished basement with a garden room and lots of storage.

3 Beds ⋅ 7 Baths

Situated on a lovely street, this very special five story townhome has it all. There are three plus bedrooms with potential for more as the top floor with an open floor plan and sunny balcony offers great flexibility. Wonderful entertaining space and formal rooms with beautiful proportions and architectural details add to the charm. A door from the living room opens out to an extraordinary deck with a balustrade. The bright, eat-in kitchen with large windows looks out on the inviting garden. Amenities include a finished basement with a garden room and lots of storage.

52 Pinckney St, Boston

Listing Courtesy of : Sally T. Brewster ---- Brewster & Berkowitz R. E.

$5,100,000

Much admired 7 bedroom, 7000+sf estate home on an acre of manicured lawns on famed Cliff Road. Built and re designed by two of New England’s most acclaimed architects, this home boasts the grandeur of stately proportions and sumptuous millwork with a newly renovated and superbly equipped chef’s Kitchen and butler’s pantry with adjacent family room. A banquet sized dining room and gracious living room both with fireplaces and french doors lead to the private grounds with stone walls, built in grill and multiple sitting areas. Handsome mahogany study with fireplace, ensuite bedroom with newly renovated bath plus a separate sun room complete the 1st floor. Up a curved staircase befitting the most prestigious of homes you will find 6 bedrooms and 4 full baths including the primary suite with, luxurious bath and laundry. Lower level with recreation room and state of the art wine cellar, 3 car heated garage, heated driveway and whole house generator. A once in a lifetime opportunity!

7 Beds ⋅ 7 Baths

Much admired 7 bedroom, 7000+sf estate home on an acre of manicured lawns on famed Cliff Road. Built and re designed by two of New England’s most acclaimed architects, this home boasts the grandeur of stately proportions and sumptuous millwork with a newly renovated and superbly equipped chef’s Kitchen and butler’s pantry with adjacent family room. A banquet sized dining room and gracious living room both with fireplaces and french doors lead to the private grounds with stone walls, built in grill and multiple sitting areas. Handsome mahogany study with fireplace, ensuite bedroom with newly renovated bath plus a separate sun room complete the 1st floor. Up a curved staircase befitting the most prestigious of homes you will find 6 bedrooms and 4 full baths including the primary suite with, luxurious bath and laundry. Lower level with recreation room and state of the art wine cellar, 3 car heated garage, heated driveway and whole house generator. A once in a lifetime opportunity!

200 Cliff Rd, Wellesley

Listing Courtesy of : Donahue Maley and Burns Team ---- Compass

$5,000,000

Nothing was overlooked in this masterfully recreated home which is a legal duplex. Perched above and overlooking the water of Mast Cove, it is only steps from Dock Square Center and all its shops and restaurants. In addition, sellers are willing to turn this property into 2 luxury condominiums for the right purchaser or leave as a legal duplex. Unit A: Approx. 1,600 sq ft featuring three ensuite bedrooms (two on the first floor, one upstairs). Unit B: Approx. 1,200 sq ft with two ensuite bedrooms. The home showcases top tier craftsmanship, award winning coastal design (2022 Down East Home Design Award), and a proven RENTAL history. Seller's willing to allow a buyer to purchase either unit individually as well--Unit A for 3,399,000 or Unit B for 1,899,000-. Enjoy this luxury living with water views, walkability to shops and restaurants, and every advantage of Kennebunkport's most desirable location. SHOWN BY APPOINTMENT ONLY AND SELLERS ARE REQUESTING A PREAPPROVAL LETTER OF FINANCING PRIOR TO OR AT ARRIVAL OF THE SHOWING. ALL CURRENT AND FUTURE RENTALS WILL BE HONORED. TAXES REFLECT THE ENTIRE PROPERTY. Condo MLS numbers are as follows: Unit A 1654913, Unit B MLS 1654909. Strong rental history.

5 Beds ⋅ 7 Baths

Nothing was overlooked in this masterfully recreated home which is a legal duplex. Perched above and overlooking the water of Mast Cove, it is only steps from Dock Square Center and all its shops and restaurants. In addition, sellers are willing to turn this property into 2 luxury condominiums for the right purchaser or leave as a legal duplex. Unit A: Approx. 1,600 sq ft featuring three ensuite bedrooms (two on the first floor, one upstairs). Unit B: Approx. 1,200 sq ft with two ensuite bedrooms. The home showcases top tier craftsmanship, award winning coastal design (2022 Down East Home Design Award), and a proven RENTAL history. Seller's willing to allow a buyer to purchase either unit individually as well--Unit A for 3,399,000 or Unit B for 1,899,000-. Enjoy this luxury living with water views, walkability to shops and restaurants, and every advantage of Kennebunkport's most desirable location. SHOWN BY APPOINTMENT ONLY AND SELLERS ARE REQUESTING A PREAPPROVAL LETTER OF FINANCING PRIOR TO OR AT ARRIVAL OF THE SHOWING. ALL CURRENT AND FUTURE RENTALS WILL BE HONORED. TAXES REFLECT THE ENTIRE PROPERTY. Condo MLS numbers are as follows: Unit A 1654913, Unit B MLS 1654909. Strong rental history.

2 Maine St, Kennebunkport

Listing courtesy of Kennebunk Beach Realty.

$5,000,000

Step inside this one-of-a-kind, recently built Victorian style home, seamlessly blending modern convenience with timeless elegance, and offering a prime location on one of the most historic sites in Lexington only steps to the town center. Whether hosting parties, guests or large family gatherings, this home will elevate your entertaining. The stunning chef’s kitchen is equipped with granite counters, 2 center islands, a breakfast bar topped with custom glass, informal dining and professional grade SS appliances including the True refrigerator and Wolf 60” gas range. Venture through the custom gazebo to the backyard, a private resort with an expansive blue stone patio, pergola, outdoor kitchen, and heated saltwater pool. The expansive primary suite has a huge walk-in closet, private balcony, fireplace and spa bathroom with glass-topped dual sink vanity, fireplace, tiled shower, and spa tub. Resort living with a pool, a movie theater, gym, and wine cellar without having to leave home!

6 Beds ⋅ 7 Baths

Step inside this one-of-a-kind, recently built Victorian style home, seamlessly blending modern convenience with timeless elegance, and offering a prime location on one of the most historic sites in Lexington only steps to the town center. Whether hosting parties, guests or large family gatherings, this home will elevate your entertaining. The stunning chef’s kitchen is equipped with granite counters, 2 center islands, a breakfast bar topped with custom glass, informal dining and professional grade SS appliances including the True refrigerator and Wolf 60” gas range. Venture through the custom gazebo to the backyard, a private resort with an expansive blue stone patio, pergola, outdoor kitchen, and heated saltwater pool. The expansive primary suite has a huge walk-in closet, private balcony, fireplace and spa bathroom with glass-topped dual sink vanity, fireplace, tiled shower, and spa tub. Resort living with a pool, a movie theater, gym, and wine cellar without having to leave home!

16 Meriam St, Lexington

Listing Courtesy of : Danielle Fleming ---- MA Properties

$4,999,999

A rare offering in the coveted Marina Heights enclave of Wentworth by the Sea. This 4,200+ SF, 4-bedroom (+office), 6-bath residence features an expansive main level with 10-foot ceilings and floor-to-ceiling windows that frame breathtaking views of the Marina and the Atlantic Ocean, and maximize the southern exposure making the living spaces light and bright. A dramatic two-story foyer welcomes you into a sun-drenched living room, which seamlessly flows into a chef-friendly kitchen anchored by a long peninsula island for gathering. The kitchen is open to the family room that features a wood-burning fireplace. Step out onto the oversized deck—the ultimate vantage point for coastal entertaining. Functionality meets style with a dedicated mudroom and separate laundry room off the attached garage, and a large pantry off the kitchen. For intimate gatherings, the dining room has a cozy, tavern inspired feel with custom built-ins, and can easily accommodate many dinner guests. Widely considered the premier floor plan in the neighborhood, the main level offers *almost* one-floor living, with the luxurious primary suite just two steps up from the living areas. It includes direct deck access, a sprawling walk-in closet, and a spa-like bath with an oversized walk-in shower, soaking tub, and a water closet with a bidet. Upstairs provides three additional bedrooms (two en suite), plus an office, an additional 3/4 bathroom, and a cedar closet. The walk-out lower level features a 6-seat wet bar, billiards area and a climate-controlled wine cellar, a dedicated space potential for a home gym and potting shed, all while maintaining direct outdoor access and ocean views. The atatched 3-car garage and exclusive access to the association pool, tennis courts, beach, and marina will seal the deal. New Castle taxes are famously low. Very walkable, bike-friendly, just minutes from downtown Portsmouth, beaches, boating, restaurants and more. Residents are prioritized for marina boat slips.

4 Beds ⋅ 6 Baths

A rare offering in the coveted Marina Heights enclave of Wentworth by the Sea. This 4,200+ SF, 4-bedroom (+office), 6-bath residence features an expansive main level with 10-foot ceilings and floor-to-ceiling windows that frame breathtaking views of the Marina and the Atlantic Ocean, and maximize the southern exposure making the living spaces light and bright. A dramatic two-story foyer welcomes you into a sun-drenched living room, which seamlessly flows into a chef-friendly kitchen anchored by a long peninsula island for gathering. The kitchen is open to the family room that features a wood-burning fireplace. Step out onto the oversized deck—the ultimate vantage point for coastal entertaining. Functionality meets style with a dedicated mudroom and separate laundry room off the attached garage, and a large pantry off the kitchen. For intimate gatherings, the dining room has a cozy, tavern inspired feel with custom built-ins, and can easily accommodate many dinner guests. Widely considered the premier floor plan in the neighborhood, the main level offers *almost* one-floor living, with the luxurious primary suite just two steps up from the living areas. It includes direct deck access, a sprawling walk-in closet, and a spa-like bath with an oversized walk-in shower, soaking tub, and a water closet with a bidet. Upstairs provides three additional bedrooms (two en suite), plus an office, an additional 3/4 bathroom, and a cedar closet. The walk-out lower level features a 6-seat wet bar, billiards area and a climate-controlled wine cellar, a dedicated space potential for a home gym and potting shed, all while maintaining direct outdoor access and ocean views. The atatched 3-car garage and exclusive access to the association pool, tennis courts, beach, and marina will seal the deal. New Castle taxes are famously low. Very walkable, bike-friendly, just minutes from downtown Portsmouth, beaches, boating, restaurants and more. Residents are prioritized for marina boat slips.

75 Marina Heights Rd, New Castle

Listing Courtesy of : Jennifer Madden ---- Gibson Sotheby's International Realty

$4,999,999

This exceptional single-family home offers impressive scale, soaring ceilings, oversized windows, and abundant natural light throughout. A gracious foyer leads to an elegant great room and adjoining music room. A curved staircase ascends to the second floor, featuring an updated kitchen with stainless steel appliances, granite countertops, a dining room, family room, and full bath. The third floor offers three spacious bedrooms and a full bath, while the fourth includes three additional bedrooms, another full bath, and laundry. The fully renovated 2023 garden level opens to a charming brick patio and includes a kitchenette and full bath—ideal for guests, an au pair, gym, or family room. The home has been thoughtfully updated, including heating and HVAC. The photos have been reimagined to showcase its potential, and with just a few cosmetic updates, this home can truly shine. Rental parking nearby.

7 Beds ⋅ 5 Baths

This exceptional single-family home offers impressive scale, soaring ceilings, oversized windows, and abundant natural light throughout. A gracious foyer leads to an elegant great room and adjoining music room. A curved staircase ascends to the second floor, featuring an updated kitchen with stainless steel appliances, granite countertops, a dining room, family room, and full bath. The third floor offers three spacious bedrooms and a full bath, while the fourth includes three additional bedrooms, another full bath, and laundry. The fully renovated 2023 garden level opens to a charming brick patio and includes a kitchenette and full bath—ideal for guests, an au pair, gym, or family room. The home has been thoughtfully updated, including heating and HVAC. The photos have been reimagined to showcase its potential, and with just a few cosmetic updates, this home can truly shine. Rental parking nearby.

18 Hereford St, Boston

Listing Courtesy of : Bill Gehan ---- Campion & Company Fine Homes Real Estate

$4,999,000

Nature Lovers Paradise on the Charles River! Stunning in every season, each element of this spectacular property is crafted to maximize your enjoyment and access to the great outdoors. Reimagined by renowned architect Patrick Ahern, the exterior boasts a flat grassy backyard and stone patios with unobstructed views. Inside, a gracious and flexible floor plan is filled with light and views from myriad windows, French doors, and private balconies. First floor living with exquisite primary bedroom suite, a great room, expansive living room, dining and updated kitchen w/ light-filled breakfast room, an add’l bedroom suite and choice of offices complete the main floor. Upstairs, 4 more ensuite bedrooms, including a 2nd primary suite option. Large walk-out finished LL w/ bar, gym & media room. 3 car garage and flat courtyard driveway off protected cul de sac within minutes of extensive Wellesley Trails and Town Center. A notch above the rest. Bring your hiking shoes, kayaks, lounge chairs and lawn games!

6 Beds ⋅ 8 Baths

Nature Lovers Paradise on the Charles River! Stunning in every season, each element of this spectacular property is crafted to maximize your enjoyment and access to the great outdoors. Reimagined by renowned architect Patrick Ahern, the exterior boasts a flat grassy backyard and stone patios with unobstructed views. Inside, a gracious and flexible floor plan is filled with light and views from myriad windows, French doors, and private balconies. First floor living with exquisite primary bedroom suite, a great room, expansive living room, dining and updated kitchen w/ light-filled breakfast room, an add’l bedroom suite and choice of offices complete the main floor. Upstairs, 4 more ensuite bedrooms, including a 2nd primary suite option. Large walk-out finished LL w/ bar, gym & media room. 3 car garage and flat courtyard driveway off protected cul de sac within minutes of extensive Wellesley Trails and Town Center. A notch above the rest. Bring your hiking shoes, kayaks, lounge chairs and lawn games!

12 Winding River Cir, Wellesley

Listing Courtesy of : Christine Lawrence ---- Rutledge Properties

$4,999,000

Own a coveted East Orleans property with a private deep-water dock on a sprawling 2.62 acres, just 2.6 miles from Nauset Beach. This estate, surrounded by water, features rolling meadows and mature trees. The 3,867 sq ft residence blends timeless charm with modern comforts. Located on Lucy's Point Peninsula, it's perfect for a family compound or riverfront retreat. Inside, enjoy wide plank pine floors, decorative fireplaces, and historic moldings. The layout offers open spaces and privacy, with four bedrooms, three bathrooms, and diverse living areas. The primary ensuite is a private wing with a sitting area and walk-in closet. The kitchen setup is ideal for culinary creativity. Entertain or relax in the nostalgic ambiance. A newer roof, heating, and AC ensure comfort. Outdoors, a versatile barn/boathouse offers recreational possibilities. Whether seeking tranquility or lively gatherings, 66 Tides End Lane welcomes you with grace and beauty.

4 Beds ⋅ 3 Baths

Own a coveted East Orleans property with a private deep-water dock on a sprawling 2.62 acres, just 2.6 miles from Nauset Beach. This estate, surrounded by water, features rolling meadows and mature trees. The 3,867 sq ft residence blends timeless charm with modern comforts. Located on Lucy's Point Peninsula, it's perfect for a family compound or riverfront retreat. Inside, enjoy wide plank pine floors, decorative fireplaces, and historic moldings. The layout offers open spaces and privacy, with four bedrooms, three bathrooms, and diverse living areas. The primary ensuite is a private wing with a sitting area and walk-in closet. The kitchen setup is ideal for culinary creativity. Entertain or relax in the nostalgic ambiance. A newer roof, heating, and AC ensure comfort. Outdoors, a versatile barn/boathouse offers recreational possibilities. Whether seeking tranquility or lively gatherings, 66 Tides End Lane welcomes you with grace and beauty.

66 Tides End Ln, Orleans

Listing Courtesy of : Cape Cod Power of Two ---- Compass

$4,998,500

Nestled on a private 0.92-acre lot in the prestigious Chestnut Hill neighborhood, this exceptional custom-designed Mid-Century Modern ranch, inspired by the timeless architecture of Frank Lloyd Wright, offers a rare blend of sophistication, privacy, and seamless indoor-outdoor living. Thoughtfully designed with gracious proportions and walls of glass, the home is filled with natural light and overlooks beautifully landscaped grounds. A spectacular four-season breakfast room with four skylights complements the chef’s kitchen featuring top-of-the-line appliances, three ovens, two dishwashers, and custom cabinetry. The luxurious primary suite serves as a private sanctuary with dual showers and vanities, smart toilets, separate dressing areas, a soaking tub, and an attached office/library. The versatile lower level offers excellent potential for an in-law suite. Sliding glass doors line the rear of the home, opening to a serene outdoor retreat with an elegant patio and heated pool. Superb

4 Beds ⋅ 5 Baths

Nestled on a private 0.92-acre lot in the prestigious Chestnut Hill neighborhood, this exceptional custom-designed Mid-Century Modern ranch, inspired by the timeless architecture of Frank Lloyd Wright, offers a rare blend of sophistication, privacy, and seamless indoor-outdoor living. Thoughtfully designed with gracious proportions and walls of glass, the home is filled with natural light and overlooks beautifully landscaped grounds. A spectacular four-season breakfast room with four skylights complements the chef’s kitchen featuring top-of-the-line appliances, three ovens, two dishwashers, and custom cabinetry. The luxurious primary suite serves as a private sanctuary with dual showers and vanities, smart toilets, separate dressing areas, a soaking tub, and an attached office/library. The versatile lower level offers excellent potential for an in-law suite. Sliding glass doors line the rear of the home, opening to a serene outdoor retreat with an elegant patio and heated pool. Superb

9 Singletree Rd, Brookline

Listing Courtesy of : Deborah M. Gordon ---- Coldwell Banker Realty - Brookline

$4,998,000

Elegance, sophistication & incredible architectural craftsmanship highlight this exquisite home, walkable to both Newton Centre & Newtonville. This contemporary colonial offers over 6900 sqft of luxurious living with 6 bedrooms & 6 full baths. The sunsplashed main level offers a formal dining, living room, office/bedroom with a 2 sided fireplace & full bath. The spacious chef's kitchen features Wolf & Subzero appliances, 2 dishwashers & 2 sinks, an island that seats 5 as well as a separate breakfast & sitting area. The inviting oversized family room with vaulted ceilings & fireplace lead out to a patio & private yard featuring an in ground pool & spa perfect for hours of entertaining. The 2nd level offers an gorgeous primary suite with a spa like bathroom & 2 walk in closets. Three additional generously sized en suite bedrooms & laundry complete this level. The finished lower level includes a spacious great room, wet bar, 2 mudrooms, bedroom, bathroom & elevator. A true masterpiece!

6 Beds ⋅ 6 Baths

Elegance, sophistication & incredible architectural craftsmanship highlight this exquisite home, walkable to both Newton Centre & Newtonville. This contemporary colonial offers over 6900 sqft of luxurious living with 6 bedrooms & 6 full baths. The sunsplashed main level offers a formal dining, living room, office/bedroom with a 2 sided fireplace & full bath. The spacious chef's kitchen features Wolf & Subzero appliances, 2 dishwashers & 2 sinks, an island that seats 5 as well as a separate breakfast & sitting area. The inviting oversized family room with vaulted ceilings & fireplace lead out to a patio & private yard featuring an in ground pool & spa perfect for hours of entertaining. The 2nd level offers an gorgeous primary suite with a spa like bathroom & 2 walk in closets. Three additional generously sized en suite bedrooms & laundry complete this level. The finished lower level includes a spacious great room, wet bar, 2 mudrooms, bedroom, bathroom & elevator. A true masterpiece!

136 Beaumont Ave, Newton

Listing Courtesy of : The Jeff Groper Group ---- Coldwell Banker Realty - Newton

$4,995,000

Experience the rare opportunity to own a timeless Cohasset Coastal Estate with sweeping Ocean Views and access to 2 Private Beaches. Originally built in 1890, this beautifully updated home has been thoughtfully renovated to preserve its architectural heritage while embracing todays sought after open concept design where the rooms seamlessly connect creating an ideal setting for both everyday living and grand entertaining. The expansive 6500+ sq ft floor plan includes 5 generous bedrooms, 4.5 baths, a Gourmet Kitchen and a sun-drenched Au Pair or In Law Suite. Large windows frame breathtaking Ocean Views bringing the beauty of the ocean into your home. Whether you are enjoying your morning coffee on one of the multiple outside decks overlooking Minot's Light or hosting a summer gathering, you will feel like you are on a permanent vacation! Designed for modern comfort, with many recent updates, this one-of-a-kind home creates a truly rare offering for those seeking luxury, privacy and a unique coastal lifestyle. A private fenced in backyard and 4 car garage are two bonuses. Appointment required.

5 Beds ⋅ 5 Baths

Experience the rare opportunity to own a timeless Cohasset Coastal Estate with sweeping Ocean Views and access to 2 Private Beaches. Originally built in 1890, this beautifully updated home has been thoughtfully renovated to preserve its architectural heritage while embracing todays sought after open concept design where the rooms seamlessly connect creating an ideal setting for both everyday living and grand entertaining. The expansive 6500+ sq ft floor plan includes 5 generous bedrooms, 4.5 baths, a Gourmet Kitchen and a sun-drenched Au Pair or In Law Suite. Large windows frame breathtaking Ocean Views bringing the beauty of the ocean into your home. Whether you are enjoying your morning coffee on one of the multiple outside decks overlooking Minot's Light or hosting a summer gathering, you will feel like you are on a permanent vacation! Designed for modern comfort, with many recent updates, this one-of-a-kind home creates a truly rare offering for those seeking luxury, privacy and a unique coastal lifestyle. A private fenced in backyard and 4 car garage are two bonuses. Appointment required.

41 Hobart Ln, Cohasset

Listing Courtesy of : Janice Crowley ---- Coastal Countryside Properties

$4,995,000

Set off a lovely cul-de-sac, this restored Greek Revival sits on 4+ acres of open field, rare this close to Boston, stretching out rather than closing in. The expansive field: open, level, and bordering the 7,000 acre Blue Hills Reservation, accessible and yours to explore. A buildable lot: room to expand, a family compound, simply hold as open space, you decide. Fine millwork and French doors speak to fine craftsmanship. The kitchen is anchored by top appliances and built for serious cooking. A well-appointed mudroom keeps the everyday beautifully managed. A glass-walled garden room with fireplace, woodland views and stillness. Modern systems (geothermal heating/cooling, solar array, EV charger) reflect a commitment to sustainability. Privacy and peace without sacrificing reach: commuter rail, Rts 128/95, and Logan Airport all close. Access to Milton's public and the area's prestigious independent schools. This is where sophistication, sanctuary, and the wide-open sky meet.

5 Beds ⋅ 5 Baths

Set off a lovely cul-de-sac, this restored Greek Revival sits on 4+ acres of open field, rare this close to Boston, stretching out rather than closing in. The expansive field: open, level, and bordering the 7,000 acre Blue Hills Reservation, accessible and yours to explore. A buildable lot: room to expand, a family compound, simply hold as open space, you decide. Fine millwork and French doors speak to fine craftsmanship. The kitchen is anchored by top appliances and built for serious cooking. A well-appointed mudroom keeps the everyday beautifully managed. A glass-walled garden room with fireplace, woodland views and stillness. Modern systems (geothermal heating/cooling, solar array, EV charger) reflect a commitment to sustainability. Privacy and peace without sacrificing reach: commuter rail, Rts 128/95, and Logan Airport all close. Access to Milton's public and the area's prestigious independent schools. This is where sophistication, sanctuary, and the wide-open sky meet.

1632 Canton Ave, Milton

Listing Courtesy of : Julianne Bridgeman ---- Ceres Real Estate

$4,995,000

Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores & restaurants & only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors & custom trim detail, beadboard ceilings, & crown molding. The home is positioned seamlessly on a large .52 acre lot with a spacious back yard, a brand new vinyl saltwater pool, outdoor shower, a screened in porch, large patio area, & an outdoor pool cabana w/ a bathroom. This home is perfect for those special summer nights on Cape Cod sitting by the pool and relaxing. Each bedroom includes it's own full bathroom including the 1st floor primary suite bedroom. A few other features added by the builder: a whole house generator, gas fireplace, irrigation system, & a 1-year builder warranty as well. Come see your dream home today before it's too late!

5 Beds ⋅ 7 Baths

Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores & restaurants & only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors & custom trim detail, beadboard ceilings, & crown molding. The home is positioned seamlessly on a large .52 acre lot with a spacious back yard, a brand new vinyl saltwater pool, outdoor shower, a screened in porch, large patio area, & an outdoor pool cabana w/ a bathroom. This home is perfect for those special summer nights on Cape Cod sitting by the pool and relaxing. Each bedroom includes it's own full bathroom including the 1st floor primary suite bedroom. A few other features added by the builder: a whole house generator, gas fireplace, irrigation system, & a 1-year builder warranty as well. Come see your dream home today before it's too late!

22 Scudder Road, Barnstable

Listing Courtesy of : The Quirk Group ---- Coldwell Banker Realty - Boston

$4,995,000

Set in one of Andover's most exclusive neighborhoods, this newly constructed estate enjoys a premier location beside The Pike School and within the prestigious Phillips Academy area—an address synonymous with distinction, academic excellence, and enduring value. Opportunities to own new construction of this caliber in such a highly regarded setting are exceedingly rare. Designed for modern living and entertaining, the home features six bedrooms, six full baths, and one half bath, offering a blend of comfort, elegance, and functionality. Expansive living spaces, architectural details, and premium finishes create an atmosphere of timeless luxury. A private first-floor guest suite with direct patio access and a mudroom with a dedicated dog wash station add convenience and flexibility. The sought-after location places residents moments from downtown Andover's dining, shopping, and commuter routes while enjoying the character of one of the town's distinguished neighborhoods.

6 Beds ⋅ 7 Baths

Set in one of Andover's most exclusive neighborhoods, this newly constructed estate enjoys a premier location beside The Pike School and within the prestigious Phillips Academy area—an address synonymous with distinction, academic excellence, and enduring value. Opportunities to own new construction of this caliber in such a highly regarded setting are exceedingly rare. Designed for modern living and entertaining, the home features six bedrooms, six full baths, and one half bath, offering a blend of comfort, elegance, and functionality. Expansive living spaces, architectural details, and premium finishes create an atmosphere of timeless luxury. A private first-floor guest suite with direct patio access and a mudroom with a dedicated dog wash station add convenience and flexibility. The sought-after location places residents moments from downtown Andover's dining, shopping, and commuter routes while enjoying the character of one of the town's distinguished neighborhoods.

7 Cider Hill Way, Andover

Listing Courtesy of : Team Lillian Montalto ---- Lillian Montalto Signature Properties

$4,995,000

Stylish Chilmark retreat with sweeping water views, private beach, tennis, and walking trails. Set within the coveted Spring Point community, this beautifully renovated island home captures a rare sense of place, with natural beauty, privacy, and effortless indoor-outdoor living. Thoughtfully updated in 2022, the home blends relaxed coastal sophistication with driftwood-colored hardwood floors, a striking stone fireplace, sleek cook’s kitchen, custom-tiled baths, and Sonos® sound. Large windows and sliding glass doors frame water views and open to private decks, while a spacious screened porch is ideal for morning coffee, summer dining, or entertaining. Landscaped grounds, a paver parking court, charming gazebo, and finished walk-out lower level add comfort and flexibility. Spring Point amenities include 68 acres of common land, ancient walking trails, two tennis courts, and Beck’s Beach, a private shoreline with magnificent sunsets from the Elizabeth Islands to Gay Head Lighthouse.

3 Beds ⋅ 3 Baths

Stylish Chilmark retreat with sweeping water views, private beach, tennis, and walking trails. Set within the coveted Spring Point community, this beautifully renovated island home captures a rare sense of place, with natural beauty, privacy, and effortless indoor-outdoor living. Thoughtfully updated in 2022, the home blends relaxed coastal sophistication with driftwood-colored hardwood floors, a striking stone fireplace, sleek cook’s kitchen, custom-tiled baths, and Sonos® sound. Large windows and sliding glass doors frame water views and open to private decks, while a spacious screened porch is ideal for morning coffee, summer dining, or entertaining. Landscaped grounds, a paver parking court, charming gazebo, and finished walk-out lower level add comfort and flexibility. Spring Point amenities include 68 acres of common land, ancient walking trails, two tennis courts, and Beck’s Beach, a private shoreline with magnificent sunsets from the Elizabeth Islands to Gay Head Lighthouse.

63 Putnam Rd, Chilmark

Listing Courtesy of : Wendy Harman ---- Compass

$4,995,000

Truly incredible offering! This elegant property with 17(!) windows on the parlor level alone, offers a private townhouse-style entrance on picturesque Spruce Street, grand spaces and 3+ bedrooms. The rooms welcome you upon entry with their allure and volume. Guests will be in awe of the expansive living and dining spaces w/ 12 foot ceilings - unique, rarely seen architecture and scale. Beautiful millwork, a gas fireplace & warm hardwood flooring all add to this graceful space. Standout features include a handsome library/home office w/ wood paneled walls-a distinguished setting. A wonderfully laid out, oversized kitchen w/ notable appliances and pantry is adjacent to a fantastic den allowing for casual dining & cozy entertaining options. A luxurious primary suite w/ seating area offers 2 walk-in closets and an opulent bathroom. Two addt'l large bedrooms w/ en suite baths, powder room, storage. Reference floorplan to view the exceptional layout of this spacious, one-of-a-kind property.

3 Beds ⋅ 4 Baths

Truly incredible offering! This elegant property with 17(!) windows on the parlor level alone, offers a private townhouse-style entrance on picturesque Spruce Street, grand spaces and 3+ bedrooms. The rooms welcome you upon entry with their allure and volume. Guests will be in awe of the expansive living and dining spaces w/ 12 foot ceilings - unique, rarely seen architecture and scale. Beautiful millwork, a gas fireplace & warm hardwood flooring all add to this graceful space. Standout features include a handsome library/home office w/ wood paneled walls-a distinguished setting. A wonderfully laid out, oversized kitchen w/ notable appliances and pantry is adjacent to a fantastic den allowing for casual dining & cozy entertaining options. A luxurious primary suite w/ seating area offers 2 walk-in closets and an opulent bathroom. Two addt'l large bedrooms w/ en suite baths, powder room, storage. Reference floorplan to view the exceptional layout of this spacious, one-of-a-kind property.

50 Beacon Street Unit 50, Boston

Listing Courtesy of : Rebecca Davis Tulman and Leslie Singleton Adam ---- Gibson Sotheby's International Realty

$4,995,000

Beautiful custom built Modern Classic home sited in a premier estate location on the south side of Weston. Designed by acclaimed architect Marcus Gleysteen and built by luxury home builder Wellen Construction this property has an absolutely enchanting setting adjacent to 30 acres of conservation land and trails. Reminiscent of a country estate in Vermont it evokes relaxed comfort with finely crafted wood details, fireplaces, a screened porch and an oversized chef's kitchen. Walls of glass showcase views of this lushly landscaped 1.4 acre ultra private lot and french doors lead to a bluestone terrace perfect for outdoor living and entertaining. Highlights include four floors of finished space, a dramatic primary suite with vaulted ceilings and a fireplace, a gym, home office and finished lower level. Nestled on a quiet cul de sac near Chestnut Street, yet offering fast access to commuting routes, top ranked public and private schools and Boston. A rare blend of prime location and charm.

5 Beds ⋅ 6 Baths

Beautiful custom built Modern Classic home sited in a premier estate location on the south side of Weston. Designed by acclaimed architect Marcus Gleysteen and built by luxury home builder Wellen Construction this property has an absolutely enchanting setting adjacent to 30 acres of conservation land and trails. Reminiscent of a country estate in Vermont it evokes relaxed comfort with finely crafted wood details, fireplaces, a screened porch and an oversized chef's kitchen. Walls of glass showcase views of this lushly landscaped 1.4 acre ultra private lot and french doors lead to a bluestone terrace perfect for outdoor living and entertaining. Highlights include four floors of finished space, a dramatic primary suite with vaulted ceilings and a fireplace, a gym, home office and finished lower level. Nestled on a quiet cul de sac near Chestnut Street, yet offering fast access to commuting routes, top ranked public and private schools and Boston. A rare blend of prime location and charm.

10 Chandler Circle, Weston

Listing Courtesy of : Rosemary McCready ---- Compass

$4,995,000

The Aldrich House returns to Red Brook Harbor. Built in 1890 as a seaside retreat for Boston travelers arriving by train, the Cataumet landmark was fully restored in 2022 with all-new systems, whole-house generator, and an 18-bedroom Title V septic, the kind of permit Cape towns no longer issue. Across three stories, more than 7,000 SF of refined interior: an open great room with floor-to-ceiling stone fireplace, a chef's kitchen, original hardwood restored throughout, and wraparound porches that hold the harbor view. 10 en-suite bedrooms, each with private sitting room, kitchenette, independent climate control, and a balcony for Buzzards Bay sunsets. Outside, 1.84 manicured acres with in-ground pool, gazebo, and firepit. The home includes 3X Commercial Speed Queen dashers and dryers, and more. Family compound, private retreat, or boutique hospitality. Minutes from sandy beaches, Red Brook walking trails, the National Seashore, and the Islands ferries; and only 80 minutes from Boston.

10 Beds ⋅ 11 Baths

The Aldrich House returns to Red Brook Harbor. Built in 1890 as a seaside retreat for Boston travelers arriving by train, the Cataumet landmark was fully restored in 2022 with all-new systems, whole-house generator, and an 18-bedroom Title V septic, the kind of permit Cape towns no longer issue. Across three stories, more than 7,000 SF of refined interior: an open great room with floor-to-ceiling stone fireplace, a chef's kitchen, original hardwood restored throughout, and wraparound porches that hold the harbor view. 10 en-suite bedrooms, each with private sitting room, kitchenette, independent climate control, and a balcony for Buzzards Bay sunsets. Outside, 1.84 manicured acres with in-ground pool, gazebo, and firepit. The home includes 3X Commercial Speed Queen dashers and dryers, and more. Family compound, private retreat, or boutique hospitality. Minutes from sandy beaches, Red Brook walking trails, the National Seashore, and the Islands ferries; and only 80 minutes from Boston.

48 Red Brook Harbor Rd, Bourne

Listing Courtesy of : Michael Carucci ---- Serhant

$4,995,000

Reimagined & redesigned stunning custom home on over 1 acre in Weston's prestigious Golf Club neighborhood. New layout, new floors, new custom built-ins, new kitchen, new butler pantry, new bathrooms, new moudings, white oak door trim, new furnaces, new AC condensers, new Marvin windows, new stone walls & landscaping...... Kitchen family room w/ breakfast nook opens to large family room w/ fireplace. Spacious living room/dining room ideal for entertaining. Private office off of grand foyer. Bedroom & en suite bath on first floor. Main bedroom w/ large custom closet & gorgeous spa-like bath. 3 additional bedrooms all w/ large closets & en suite baths. Front & back staircase. 2 mudrooms. Lower level w/ full bath, playroom, media room plus exercise. This home has huge Marvin windows creating a sunfilled home. Overlooking majestic Skating Pond & its rustic lodge designed by Fredrick Law Olmstead in 1909. Close distance to Weston Town Center and routes to Boston. A must see!

5 Beds ⋅ 8 Baths

Reimagined & redesigned stunning custom home on over 1 acre in Weston's prestigious Golf Club neighborhood. New layout, new floors, new custom built-ins, new kitchen, new butler pantry, new bathrooms, new moudings, white oak door trim, new furnaces, new AC condensers, new Marvin windows, new stone walls & landscaping...... Kitchen family room w/ breakfast nook opens to large family room w/ fireplace. Spacious living room/dining room ideal for entertaining. Private office off of grand foyer. Bedroom & en suite bath on first floor. Main bedroom w/ large custom closet & gorgeous spa-like bath. 3 additional bedrooms all w/ large closets & en suite baths. Front & back staircase. 2 mudrooms. Lower level w/ full bath, playroom, media room plus exercise. This home has huge Marvin windows creating a sunfilled home. Overlooking majestic Skating Pond & its rustic lodge designed by Fredrick Law Olmstead in 1909. Close distance to Weston Town Center and routes to Boston. A must see!

9 Skating Pond Road, Weston

Listing Courtesy of : Melissa Dailey ---- Coldwell Banker Realty - Wellesley

$4,995,000

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace—ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.

4 Beds ⋅ 5 Baths

CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace—ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.

205 South Rd, Chilmark

Listing Courtesy of : Tina Miller ---- Donnelly + Co.

$4,995,000

LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, beautifully blends elegance and comfort. The open floor plan features oversized windows and soaring ceilings, offering illuminating views of the swimming pool, spa, outdoor kitchen, patio, gas fire pit, and an irrigated, fenced-in lawn. Ownership includes deeded neighborhood access to Lighthouse Beach. The gourmet kitchen seamlessly integrates the dining room, custom bar, pantry, and wine storage. The inviting living room features a cozy fireplace. The fifth bedroom has been thoughtfully transformed into an inspiring study. On the second floor, you’ll find four wonderfully proportioned bedrooms, each offering distant views of the Atlantic Ocean, and three stylish full bathrooms. The primary suite is a true retreat, boasting a spacious walk-in closet, a dressing room, and an exquisite bath. Main St, Chatham, is less than a mile, and nearby Outermost Harbor is a boater's dream marina.

4 Beds ⋅ 5 Baths

LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, beautifully blends elegance and comfort. The open floor plan features oversized windows and soaring ceilings, offering illuminating views of the swimming pool, spa, outdoor kitchen, patio, gas fire pit, and an irrigated, fenced-in lawn. Ownership includes deeded neighborhood access to Lighthouse Beach. The gourmet kitchen seamlessly integrates the dining room, custom bar, pantry, and wine storage. The inviting living room features a cozy fireplace. The fifth bedroom has been thoughtfully transformed into an inspiring study. On the second floor, you’ll find four wonderfully proportioned bedrooms, each offering distant views of the Atlantic Ocean, and three stylish full bathrooms. The primary suite is a true retreat, boasting a spacious walk-in closet, a dressing room, and an exquisite bath. Main St, Chatham, is less than a mile, and nearby Outermost Harbor is a boater's dream marina.

101 Morris Island Rd, Chatham

Listing Courtesy of : The Bohman Hartung Group ---- Gibson Sotheby's International Realty

$4,995,000

The Ultimate Newton Location 1/2 block from Waban Square! Have you been dreaming of working with a respected local design firm to realize your vision of a contemporary home equipped with a chef's kitchen? If you need an expansive home office on a separate level with privacy, comfort and a safe distance from the refrigerator this house has it! This charming village home is a modern masterpiece designed for discerning taste. Top rated schools, convenient public transit and strategic location near all major roadways make this the ideal option for your new home! The builder has their own model home custom build studio, and they will build this house to your exact specifications...but you need to act quickly before the work begins. Expect occupancy in the Summer of 2026.

6 Beds ⋅ 8 Baths

The Ultimate Newton Location 1/2 block from Waban Square! Have you been dreaming of working with a respected local design firm to realize your vision of a contemporary home equipped with a chef's kitchen? If you need an expansive home office on a separate level with privacy, comfort and a safe distance from the refrigerator this house has it! This charming village home is a modern masterpiece designed for discerning taste. Top rated schools, convenient public transit and strategic location near all major roadways make this the ideal option for your new home! The builder has their own model home custom build studio, and they will build this house to your exact specifications...but you need to act quickly before the work begins. Expect occupancy in the Summer of 2026.

151 Pine Ridge Road, Newton

Listing Courtesy of : James Lowenstern ---- eXp Realty